Water → 5-Hydroxy-3,3-dimethylisoindolin-1-one

HRID 1737309노트

반응식

HRID 1737309 반응식
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[NH:11][C:10]2([CH3:18])[CH3:17].O>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[NH:11][C:10]2([CH3:18])[CH3:17]

참가 물질

5

반응물 3

HCID 962WaterHCID 25134Boron tribromide2회HCID 105838765-Methoxy-3,3-dimethylisoindolin-1-one

생성물 1

HCID 107736505-Hydroxy-3,3-dimethylisoindolin-1-one수율 57%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

A 1 M solution of BBr3 in CH2Cl2 (88.0 mL, 88.0 mmol) is dissolved in dry CH2Cl2 under N2. A solution of lactam 57 (7.65 g, 40.0 mmol) in CH2Cl2 (50 mL) is added to the BBr3 solution dropwise over 10 min. The resulting mixture is stirred at rt overnight. The reaction mixture is poured into water and extracted with EtOAc (3×). The organic phase is dried (MgSO4), filtered, and evaporated, leaving the product 62 as a white solid (4.03 g, 57%), mp 231-233° C., which requires no purification. 1H NMR (DMSO-d6, 2.50 ppm) 8.18 (s, 1), 7.28 (d, 1, J=8.5), 6.75 (d, 1, J=1.6), 6.67 (dd, 1, J=8.5, 1.6), 1.25 (s, 6); 13C NMR (CDCl3 +DMSO-d6) 169.30, 161.06, 155.40, 124.68, 121.53, 115.39, 107.26, 57.98, 27.47; MS (MW=177.2, EI, eE=70 eV) m/z 177 (M+), 163, 162 (base peak).

후처리

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe organic phase is dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

출처 및 근거

ORD 기록
ord-39a30563791d41c6910336e63557c569
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962469

반응 노트

불러오는 중…